N-[2-(3,5-dichloropyridin-2-yl)-2-(ethoxyimino)ethyl]-2-(trifluoromethyl)benzamide → N-[(2Z)-2-(3,5-dichloro-2-pyridinyl)-2-ethoxyiminoethyl]-2-(trifluoromethyl)benzamide

HRID 55981Notes

Reaction equation

HRID 55981 reaction equation
[Cl:1][C:2]1[C:3]([C:9](=[N:24][O:25][CH2:26][CH3:27])[CH2:10][NH:11][C:12](=[O:23])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]([F:22])([F:21])[F:20])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1>C(#N)C>[Cl:1][C:2]1[C:3](/[C:9](=[N:24]\[O:25][CH2:26][CH3:27])/[CH2:10][NH:11][C:12](=[O:23])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]([F:21])([F:20])[F:22])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

3

Reactant 1

HCID 131736883N-[2-(3,5-dichloropyridin-2-yl)-2-(ethoxyimino)ethyl]-2-(trifluoromethyl)benzamide

Product 1

HCID 118071503N-[(2Z)-2-(3,5-dichloro-2-pyridinyl)-2-ethoxyiminoethyl]-2-(trifluoromethyl)benzamideYield 21.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

190 mg of N-[2-(3,5-dichloropyridin-2-yl)-2-(ethoxyimino)ethyl]-2-(trifluoromethyl)benzamide was dissolved in 4 ml of acetonitrile, and the solution was irradiated with light for 2.5 hours in a quartz cell (manufactured by Fine, 4 clear windows for spectroscopy) using a 100 W high-pressure mercury lamp (manufactured by USHIO INC., lamp: UM-102, power supply: UM-103B-B). After completion of the reaction, the solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography using ethyl acetate-hexane (with a gradient of from 1:9 to 3:7) as the eluent to obtain 41.3 mg of the desired product as white crystals.

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was evaporated under reduced pressure
  3. customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-14fcdf7ccf6e4475804e6698de7f0131
Source dataset
uspto-grants-2016_09
Patent number
US09434684B2

Reaction notes

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